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Distance to beach: 3 miles to Sombrero
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Plan your Marathon Trip - Stay at Manatee Cove-4BR/2BA vacation home. Pool with Spa, Tiki, Quick Atlantic access!Escape to the Florida Keys ~ Gorgeous 4BR/2BA Home on the Atlantic side of the canal in Marathon. Our home offers the best pool in our area; who can say no to a hot tub, pool, and bar stools...
Featured review
My family and I had a wonderful week here. The owner and property manager were both a pleasure to work with. Our favorite amenity was the pool and hot tub. We had plenty of space and all of the beds were...
Distance to beach: 0.1 miles to Sombrero Beach
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Waterfront 6 Bedrooms , 5 Baths, canal views. On the HIGHLY sought after Sombrero Beach !!!(We rent weekly only, and our Check-in is on a Saturday and Check-out is on a Saturday dates only so we can optimize our months.)Our houses are safe and clean because we disinfect them with the highest...
Featured review
The house was very clean, and location could not be better. The house was more amazing than the pictures showed. The outside tiki hut, (2) barbeque grills and pool made a perfect end to a day of fishing....
Distance to beach: 1 miles to Sombrero Beach
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Weekly rentals in the Keys {and generally elsewhere } are based on a Saturday to Saturday occupancy. Check - in is on Saturday at 4:00 PM, and check - out is on the following Saturday at 9:00 AM. Check in directions are emailed to you the week prior to your arrival { please check "spam" } Pups...
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Gulf-Front Modern Luxury | 5BR w/ Rooftop Deck, Infinity Pool, Dock & More! Indulge in an unparalleled luxury experience in this breathtaking 5-bedroom, 5.5-bathroom estate in Marathon, Florida. With direct Gulf views, high-end amenities, and a sleek modern design, this home is a dream getaway for...
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Blue Turtle Villa at The Tides of Vaca Cut (Unit #4), is a brand new 5 bedroom 4 bath home with a private pool, boat slip, all the toys for the perfect vacation ~ paddle boards, kayak, giant Jenga, giant connect four, ping pong and more! Perfectly situated on the water with stunning views, sunrise and...
Featured review
The home is absolutely beautiful and in a great location, beautiful views and has all the amenities needed for a great family vacation!
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Welcome to 137 Mockingbird Cove! Modern, expansive home built in 2022, offering incomparable boating! Quick walk or ride from Sombrero Beach. Each of the 5 bedrooms features its own ensuite bathroom, offering ultimate privacy and comfort. Includes a private heated/chilled pool, 2 paddleboards, 4 bicycles,...
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MARATHON ANGLER'S RETREAT in Marathon is a brand new property with every modern convenience and warm coastal decor! Located right on a canal (just 15-20 minutes from open water) it has its own private dock (can accommodate up to a 30' boat), fish cleaning station, private pool, hot tub, and...
Featured review
Meredith and Pineapple Properties were very accommodating, and answered all of our questions. The home, the pool, and the hot tub are all in great working shape, well-maintained, and clean. The property...
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Gulf side Gem, 45 ft. Dock, pool , hot tub and moreSpacious 3 Bedrooms and 3 Baths 1,600 sq ft home overlooking a canal with a brand new dock that spans the width of the property complete with a fish cleaning station and private pool and brand new hot tub. The Open Concept Living and Kitchen Area...
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SALT & SKY has 4 bedrooms and 3 full bathrooms, sleeps 10 (including infants and children) - Upstairs Master w/ king & en suite bathroom - 1 guest room downstairs w/ queen size bed - A full bath is located on the first floor. Perfect for individuals who have trouble navigating stairs. - 2...
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Casa Feliz~ Experience, enjoy, relax, and rejuvenate in luxury accommodations on the Atlantic Ocean.~ Secluded sophistication can be your vacation destination.Welcome to Casa Feliz! We are located on the quiet Grassy Key in the middle of the Florida Keys.Concierge Level Luxury vacation...
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Welcome to your perfect tropical getaway! This stunning, completely remodeled half duplex in Key Colony Beach offers a blend of modern luxury and coastal charm. From top to bottom, no detail has been overlooked in creating this immaculate vacation retreat.Relax and unwind in the spacious living areas...
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"The furnishings/decor are beautiful. This is one of the nicest houses we have had the pleasure to rent, everything is spotless/brand new. It was hard getting our kids ages 8 and 10 to leave the house each day for adventures. " -Kristie KruegerAs a boating enthusiast, I designed Captain's...
Distance to beach: 4 miles to Sombrero Beach
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Come stay with us! Why?68 FIVE STAR reviews!! It's literally the highest number of reviews for ALL properties listed here on !!! That's right ALL OF THEM!Welcome to the luxurious “Yellowtail” Villa, where luxury meets the Gulf of Mexico! The only problem with this vacation...
Featured review
We had a great week in paradise! The rooftop was AMAZING. Everything was labeled which made finding what.you needed a breeze. We can't wait to come back!
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Villa Sombrero – Private Waterfront Living with Sunset Views in the Florida KeysVilla Sombrero is a peaceful waterfront retreat overlooking Boot Key Harbor, offering breathtaking sunsets to the west and refreshing island breezes flowing in from the east through Sisters Creek. A natural waterway...
Featured review
We really enjoyed the house, very well appointed! 5 kayaks for you to use anytime , and believe me we used them and had a blast! Debra the owner is a dream even had a Bottlle of Champaign and a cake waiting...
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Forget your worries in this spacious and serene space. Enjoy all that Marathon has to offer in this perfect location within walking distance to Cocoplum beach. This spacious completely renovated 2 bedroom condo offers everything that you will need for your vacation rental. Offering a boat slip right outside...
Featured review
Fantastic condo in Marathon. Great location with its own community boat ramp, a dock right next to the condo, a pool, and a nice sandy beach a very short walk away. The best part was Katie Carillo the realtor...
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Updated two bedroom, two bathroom half duplex on 11th street. Excellent location towards the end of the canal yielding instant access to Vaca Cut and the Open Atlantic, 37 ft of deepwater dockage on an extra wide canal is perfect for fisherman and families alike! Enter through the street-side screened...
Distance to beach: 0.1 miles to On site
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BEST SUNSETS in the Keys, Key Colony Point unit #15, Ocean Beach Front, 2 bedroom, 2 bath ensuite, newly remodeled Condo with new furniture.COMPLEX: KEY COLONY POINT UNIT #15 Perfect get away for a week or a month.BEACH is 30 feet from our balcony. 150 feet to pool with hot tub. Great fishing...
Featured review
Absolutely the best view and pool in Key Colony. Spacious and well appointed condo. Would repeat #15 Very quiet and relaxing without crowds and annoying children!
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DOCKSIDE RETREAT is a 4 bedroom 3 bath canal front home that has a private pool, private dock, fish cleaning station, with a green light under the dock, two paddle boards, a kayak, four bikes, and a Tiki Hut for the ultimate Keys vacation! There are 4 parking spots for vehicles and one boat trailer (you...
Featured review
We had a fabulous stay in your property. We really appreciated all of your amenities. We love to cook some of our meals in and you had a great selection of pots and pans and dinnerware. We also like...
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2 bedrooms, 2 bathrooms ideal getaway in Coco Plum Beach, the Florida Keys. Great value and our reviews are excellent! Small Pets OK for downstairs unit.We have two units in the same building.Amazing amenities, that include waterfront swimming pool, boat dockage included for boat up to 40’,...
Featured review
Beautiful condo, great amenities with pool, boat dockage, launch, and trailer parking! Condo is spacious, great decorations, and very comfortable. Everything you need for a wonderful 5 week vacation....
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VACA-22-238 BRAND NEW BUILD! 3- bedrooms with king beds and full size bathrooms, and 1/2 bath for guests. Large common area living room and open kitchen. Located on canal three houses from the ocean, with great open water views. Pool with sitting area under the house. Our home offers a 60'...
Featured review
This home is perfect for a vacation. It is super clean and everything in the home is new. The home is also stocked with anything you could need for your stay. The location is great, and the views are breathtaking....
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Mar Azul is a High-end Oceanfront Residence overlooking the tranquil 'Bonefish Flats' of Marathon. Enjoy a Private, Secluded 3-Story Home with Spectacular Views of the Atlantic Ocean! Densely surrounded by Nature, the Property includes a Private In-Ground Pool Deck featuring an Outdoor Gazebo...
Featured review
Mar Azul is in a perfect location, accessible to many great restaurants, shops and and one of the best beaches in Marathon, Sombrero Beach. The home is comfortable and serene, with two ensuites! The decks...
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Tingler Retreat is a tastefully decorated 3 bedroom, 3 bath home with a pull-out couch, has a peek-a-boo view of the ocean and is seconds to open water in your boat! It has an open floor plan and is ground level with plenty of natural light and a fully fenced yard! Available for guest use are 2 bikes,...
Featured review
My husband and I hosted our daughter, son in law and 2 grandkids for a week. They loved the pool and the closeness to sombrero beach. It’s at nice quiet neighborhood with a lot of parking. The house is...
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"SOMBRERO HEAVEN" is a canal front 4 bedroom 3 bath attached Villa with neighborhood ocean front beach just down the street! It has a private pool that can be heated or chilled (for a fee), private dock (up to 35' boat), fish cleaning station, bait freezer and 4 new bikes! Additionally,...
Featured review
Meredith is prompt and helpful. Everything you could want at the beach or for your boat is provided. This is a big plus if flying in. Hope to return here. Highly recommend!
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Sun Kissed Tails is a beautiful 3 bedroom 3 bath townhome, with a modern coastal feel, in the Hawks Cay resort on Duck Key, MM61.ENJOY THE POOL AND BEACH AT THE OCEAN FRONT CABANA CLUB, just a 15 min drive to Key Colony Beach. The Cabana Club has an olympic size pool, Tiki Bar and restaurant, ocean...
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Stunning rooftop views from this gulf side Tuscan style Villa3 Bedroom 3 Bathroom Freestanding villa located in Bougainvillea, a Gated Community, with a pool exclusive to Bougainvillea Clients overlooking The Gulf of Mexico.There is Great Fishing at this location! You can bring your boat in for...
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We would love for you to come visit our renovated ground level Florida Keys home! We decided to call our home "TIGHT LINES", because my wife loves to fish. Our conch home consists of 3 bedrooms with king size beds with ensuite bathrooms. A half bath for guests. We have a 60 foot dock with...
Featured review
I can’t say enough about this property and the owners. From the ease of booking to our entire stay, we were more than happy. The home is top notch, great beds and very well stocked. The owners were...
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Blue Shell is a delightful new canal front vacation home with a pool, just a minute to the ocean and open water and lots of fun amenities! It is also about 10 minutes from both Coco Plum Beach and Sombrero Beach.The dock is 50' and there is parking on the side of the house for truck and trailer....
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Elegant Florida Keys direct ocean access and some open water views from the dock and balcony. This property is single family elevated home. All rooms and bathrooms are upstairs. 40 foot dock with 4 cleats. Large driveway, parking for at least 6 cars, trailer and RV. 75' of waterfront with wood dock....
Featured review
Can’t say enough about Maria and Daniel the owners. They catered to us from first contact. The place was spotless and the home is even nicer than the pictures. It was a short visit for my wife and I,...
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Welcome to our waterfront family home located in a quiet, yet friendly gated community in Marathon, Florida! If you’re looking for a relaxing and low-energy getaway for your family, you’ve found the perfect place.Consider a 14-day stay and receive an 8% discount OR 28-day stay and receive...
Featured review
The property was amazing the views of the water were fantastic. The dock area was super great for fishing off of every day. The elevator was a life savior for getting suit cases and groceries up stairs....
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Pineapple Tides, located at "The Tides at Vaca Cut" (Unit #8), is a new 5 bedroom 4 bath home with a private pool and boat slip!Perfectly situated on the water with stunning views, sunrise and sunset colors, and direct quick access to both the Atlantic Ocean and the Gulf of Mexico via Vaca...
Distance to beach: 3 miles to Sombrero Beach
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This charming oceanfront property is the perfect getaway for your next vacation. Located just steps away from the ocean, this cozy retreat features stunning views, modern amenities, and a spacious deck for outdoor relaxation. Enjoy the convenience of nearby shops, restaurants, and attractions. Book your...
Featured review
Newer, modern, comfortable, and well decorated oceanfront property. Had everything we needed and more. Beautiful views from the deck and very nice outside area. We appreciated that there were great...
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Tropical Canalfront Retreat Near Sombrero Beach – 2 Bed / 2 BathEscape to paradise at this beautifully appointed 2-bedroom, 2-bathroom vacation home located in the heart of Marathon, Florida. Nestled on a deep, wide canal, this waterfront getaway offers the perfect blend of comfort, convenience,...
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This 3 bedroom, 2.5 bath single-family modern home is great for entertaining! Enjoy the outdoor area with a pool and a separate hot tub or catch a game of pool on the main floor. This home is located on the 63rd Street canal and being ocean-side, it's just a quick trip out to sea where you'll...
Featured review
Spent Thanksgiving week at The Keys Retreat. Perfect location, house was very clean and kitchen stocked with everything you need. Really enjoyed the outside area in the pool and jacuzzi.
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Welcome to our private stand-alone oceanfront home in a quiet, yet friendly gated community in Marathon, Florida! If you’re looking for a relaxing and low-energy getaway for your family, you’ve found the perfect place.Consider a 14-day stay and receive an 8% discount OR 28-day stay and...
Featured review
In summary, fabulous views! From the roof you get both the Atlantic and gulf. Unobstructed 180 degree gulf view. The house is great too. Everything you need to sleep comfortably, relax, cook. Space for...
Distance to beach: 1 miles to Sunset Park
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Family-friendly Waterfront Oasis with Private Heated Lazy River Pool and 70' Dock Summary: Welcome to Your Dream Florida Keys Getaway! Bring the family to experience the ultimate Florida Keys vacation! Nestled in family-friendly Marathon—right in the heart of the Keys—our...
Featured review
We could not have asked for a better place to stay. The hosts were absolutely amazing. The lazy river pool was our favorite place to be. The grill ran out of propane one night and we messaged the host and...
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Sailfish Villa, unit #6, is a brand new gorgeous, professionally decorated 5 bedroom 4 bath Villa with open water views on Vaca Cut! Enjoy sunrise and sunset colors and direct ocean and Gulf access! It has a private pool and boat slip for a boat up to 35' including motors. There is no additional...
Featured review
I have been coming to marathon with family for many years and have had many rentals.. Meredith I have to say is the best.. she worked with me with every question and plans that I had . Definitely would...
Distance to beach: 2 miles to Sombrero Beach
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Our waterfront, single-family home, affectionately named “Turtle Cove”, offers 3 bedrooms, 2 baths, and and dockage with quick ocean access! This tastefully furnished Keys home is located on a quiet side street in a residential neighborhood on the Atlantic side of the Island, just 5 houses...
Featured review
We love to stay in the Keys & this was a perfect retreat! The home was clean & cozy! The pool was private & secluded from the neighbors as well was the hot tub. Beautiful canal view & very quiet location...
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Reel Life 2 has everything! 4 bedroom 3 bathrooms, canal front, private dock (boat up to 35'), large private pool, Tiki Hut with flat screen TV, large grill, 2 bikes, 2 paddle boards, 1 kayak and a natural landscape view across the canal! Plus, Sombrero Beach is just down the street (1.3 miles)....
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Welcome to Turtles Nest! A beautiful 2-bedroom 2 bath condo in the heart of Marathon complete with 40' boat slip and a private boat ramp! 30 steps to the water and heated pool, this 2/2 condo is ready for your changes in attitudes, changes in latitudes!Community/Location: - beautiful canal-front...
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Come have your first sunset drinks compliments on us at Island Fish Company. $100 Gift Certificate to Island Fish Company Included. No Expense Spared! New Construction Bayfront Home With Private Dock and Pool.5 O'Clock Somewhere Bay House is a piece of paradise on the Vaca Cut waterway in Marathon....
Featured review
This vacation getaway home had everything we needed plus Lauri was an extremely responsive host. The location was excellent. We could walk to the Aquarium that was across the canal or drive ten minutes...
Distance to beach: 1 miles to Sombrero Beach
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Embark on an idyllic getaway to our spacious 4-bedroom, 3-bathroom vacation villa nestled in Marathon, the heart of the Florida Keys. Escape to Stay Anchored, where tranquility meets luxury. Boasting a prime location on a spacious canal, our retreat features a private heated and chilled pool, inviting...
Featured review
Stay anchored at Sombrero was an amazing property....The location was perfect for our group. The house is very comfortable and welcoming. The property owners are exceptional responding promptly to any...
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Welcome to Your Private Oceanfront Oasis in Marathon, Florida!Discover an unparalleled retreat in the heart of the Florida Keys where every day begins with breathtaking sunrises over turquoise waters. This charming oceanfront cottage effortlessly blends a relaxed beach vibe with upscale comforts,...
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"Wow beyond wow! This place had everything we needed and more. We like to rent a house where we can spend most of our time there enjoying family time. The pool and all the games with the game room and infinity table and the dining turned ping pong was amazing. Eric was very responsive..." -...
Featured review
The place In Marathon was great !!! It had everything you needed pool the canal to watch the manatee go by close proximity to everything !! The only complaint I would have is TVs in 2 of the 3 bedrooms...
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Come enjoy this beautiful OCEAN VIEW condo located in Key Colony Beach on the 2nd floor!!! This two bedroom & two bathroom condo offers all the amenities of home!!! Enjoy a cup of coffee in the morning, or a glass of wine anytime on one of the two ocean view balconies. Coin laundry right outside the...
Distance to beach: 1 miles to cocoplum
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Are you ready to Seas the Day? 30 steps to the water and heated pool, this completely renovated 2/2 condo is ready for your changes in attitudes, changes in latitudes!Community/Location: - beautiful canal-front community - steps from heated (and chilled) saltwater pool (easier on eyes, skin and...
Distance to beach: 1 miles to Sombrerro Beach
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Lemon Key CottageWelcome home…Thanks to Hurricane Irma, we now have a beautiful newly renovated home! We've spent over $150K on a complete restoration and modernization. (check out the new pics) Lemon Key Cottage is absolutely stunning with new: bathrooms, kitchen, appliances, flooring,...
Featured review
10 ️ Rating! I called Florida Rentals. I Booked. Counted Down the days until our Christmas vacation began. We were able to take homemade cookies to the USCG base on Christmas Day. We were able to see...
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This beautiful 4 bedroom, 3 bath home is less than 2 minutes from Sombrero Beach just down the street (oceanfront) and less than 15 minutes to open water! Although there are two attached units, each have their own private amenities and parking. There is a private pool with outdoor tv on the patio, private...
Featured review
Excellent stay, everything in the house worked smoothly, nice big pool, kayaks at our disposal, Sombrero beach, groceries in just few minutes of drive. One ctisism: no garbage recycling option.
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Welcome to your spacious, five-bedroom waterfront pool home in Marathon, just steps from Sombrero Beach! Enjoy multiple entertaining areas inside and out, with a screened-in patio and sparkling pool (pool heat available for an extra fee). The open-concept interior features cathedral ceilings, a modern...
Distance to beach: 100 yards to Sombrero Beach
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Seaside Sandpiper is truly a unique property that can accommodate as few guests as you want and up to 30! Rent the 6 bedroom main house by itself or rent the entire 14 Bedroom Main house and Addition! Weddings, family reunions and business retreats are all possible at our home! Our pet friendly home...
Distance to beach: 4 miles to Sombrero Beach
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New construction! This spacious and tropically decorated property includes 4 KING bedrooms, each with private ensuite bathrooms. There is an additional half bath for guest use, as well as commercial washer and dryer. State of the art kitchen with quartz counter tops and well appointed living area including...
Featured review
We stayed at Niki's Kraken's Cove mid-February 2026. It was the perfect place for four couples in their 50s. All 4 bedrooms are similar with King size beds and ensuite bathrooms. The beds & bedding were...
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